Methyl p-coumarate, a melanin formation inhibitor in B16 mouse melanoma cells

Bioorg Med Chem. 2004 Oct 15;12(20):5349-54. doi: 10.1016/j.bmc.2004.07.052.

Abstract

p-Coumaric acid (4-hydroxycinnamic acid) and methyl p-coumarate (methyl 4-hydroxycinnamate) inhibit the oxidation of L-tyrosine catalyzed by mushroom tyrosinase. However, both were oxidized as monophenol substrate analogues at an extremely slow rate. This oxidation was significantly accelerated as soon as catalytic amounts (0.01 mM) of L-3,4-dihydroxyphenylalanine (L-DOPA) became available as a co-factor. Methyl p-coumarate significantly suppressed the melanin formation in B16 mouse melanoma cells, whereas p-coumaric acid did not show this activity.

MeSH terms

  • Animals
  • Coumaric Acids / chemistry
  • Coumaric Acids / pharmacology
  • Melanins / biosynthesis*
  • Melanoma, Experimental
  • Mice
  • Propionates
  • Tumor Cells, Cultured
  • Tyrosine / metabolism

Substances

  • Coumaric Acids
  • Melanins
  • Propionates
  • Tyrosine
  • p-coumaric acid